Wondering about selling? Let me ask a few questions.
May 12, 2026 •
I talk to business owners all the time who tell me they’re ready to exit. Forty years in the trades, body’s tired, they’ve seen other owners retire.
So I ask a simple question: What have you put into place that makes you feel ready?
And the answer is often the same. “The business is doing well. We’ve got the revenue, the trucks, the team. Someone’s going to want this.”
But wanting to sell and being ready to sell are two very different things.
If you’re three to five years out, here are the questions I’d want you to spend some time with:
Can your business run without you?
If you’re the only person who knows how to do everything, that may affect what the business is worth to a buyer. That means thinking about building a team now that can run things without you, and that typically takes years, not months.
Do you know what you’re actually taking home?
A sale price and what you actually take home can look very different once you account for taxes. What does the business need to be worth? What are the tax implications? Those are questions worth working through with your advisory team, not figuring out after a check lands on the kitchen table.
Are all your advisors talking to each other?
Lots of business owners I meet have someone in each seat: Accountant, attorney, insurance, financial advisor. But in many cases, nobody is talking to each other.
In a silo, they may each be doing a good job. In our experience, though, when everyone is coordinated and working together on behalf of the business owner, things can run more smoothly, more coordinated, and more on track with the owner’s goals.
What are you doing the morning after the exit?
In our experience working with owners who’ve been through this, within a few months of stopping, the novelty can wear off fast, and the lack of routine can be harder than anyone expected.
You may want to think about purpose on the other side. Consider taking a few months off before you fully exit. Dip your toe in. See what it feels like before you’re locked into it.
In my experience, the path to financial security after an exit doesn’t have to be as complicated as most owners fear, but it does take planning, the right team, and time.
That work doesn’t start the day someone slides a check across the table.
It starts three to five years before.
— Michael
Interested in how this works? Let’s talk.
Book a JobWalk with me and we can start the conversation.
Interested in other Rungs? Check out:
- The full Ladder here or the audio edition here
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HFM Investment Advisors, LLC is a registered investment adviser. All statements and opinions expressed are based upon information considered reliable although it should not be relied upon as such. Any statements or opinions are subject to change without notice. Information presented is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any specific securities, investments, or investment strategies. All investments involve risk and are not guaranteed. Information expressed does not take into account your specific situation or objectives and is not intended as a recommendation appropriate for any individual. Listeners are encouraged to seek advice from a qualified tax, legal, or investment advisor to determine whether any information presented may be suitable for their specific situation. Past performance is not indicative of future performance.
